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D-Norvaline, Also known as D-normal valine or (R) - (-) -2-aminovaleric acid, it is an important amino acid derivative, especially occupying a place in the application of pharmaceutical intermediates. The appearance is white to almost white crystalline powder, with a molecular formula of C5H11NO2, CAS 2013-12-9, and a molecular weight of 117.146. It has a certain solubility in both polar solvents (such as water) and non-polar solvents.
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Chemical Formula |
C5H11NO2 |
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Exact Mass |
117 |
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Molecular Weight |
117 |
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m/z |
117 (100.0%), 118 (5.4%) |
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Elemental Analysis |
C, 51.26; H, 9.46; N, 11.96; O, 27.31 |
However, due to its relatively low solubility in water, organic solvents are often used for dissolution in practical applications. It also has certain application potential in other fields. For example, in the cosmetics industry, it can be added as moisturizing agents, antioxidants, and other ingredients to skincare products to improve the skin's water retention and antioxidant capacity. In addition, it can also be used to manufacture some special chemicals and materials.
D-Norvaline, D-n-valine, as a non natural amino acid, plays an important role in scientific research and experimentation due to its unique molecular structure and biological activity. It not only serves as a pharmaceutical intermediate and participates in the synthesis of various drugs, but also has broad application value in multiple fields such as biology, medicine, and nutrition.
1. Application in biological research
Research on Amino Acid Metabolism
As a type of amino acd, its metabolic pathways and mechanisms are of great significance for understanding the overall process of amino acd metabolism in organisms. Researchers can use isotope labeled products to track their metabolic pathways in organisms and reveal the regulatory mechanisms of amino acd metabolism.
Research on Protein Synthesis
It can participate in the process of protein synthesis and affect the structure and function of proteins. Researchers can observe the effect of adding this substance to the in vitro experimental system on protein synthesis and explore the regulatory mechanism of protein synthesis.
It has a wide range of applications in cell experiments. For example, in cell culture experiments, it can serve as an energy supplement that affects the secretion of synthetic metabolic hormones, fuel supply during exercise, and mental performance during stress related tasks. Researchers can observe the effects of adding different concentrations of this substance on cell growth, metabolism, signal transduction, and other aspects, thereby revealing its biological effects and mechanisms.
Application in medical research
Drug development
As a pharmaceutical intermediate, it can participate in the synthesis of various drugs. Researchers can use this substance as a raw material to synthesize drug molecules with specific biological activities, and then develop new drugs with therapeutic effects. For example, perindopril, as an effective drug for treating hypertension and heart failure, is synthesized with L-normal as an important intermediate.
Disease model construction
It can be used to construct specific disease models, such as metabolic diseases, neurological diseases, etc. By adding this substance to experimental animals or cell lines, simulating amino acd metabolism abnormalities in disease states, and studying the pathogenesis and treatment strategies of diseases.
Pharmacodynamic evaluation
There are locations in the United states of america as well as ationally. The organization was established in 2000 on the basis of a small idea conceived by its promoters that was incepted.
Application in Nutritional Research
Nutritional Supplements
The product and its structural analogues have emerged as promising components in the formulation of specialized nutritional supplements, particularly targeting populations with high energy demands and metabolic regulation needs. Commercially available supplements leverage it's unique metabolic properties to enhance physical performance and support recovery-making it a key ingredient for athletes, fitness enthusiasts, and busy professionals.
In sports nutrition, the product acts as a metabolic modulator that optimizes energy utilization during intense activity. By influencing the activity of branched-chain amino acid (BCAA) transporters and reducing muscle protein breakdown, it helps delay fatigue during endurance exercises (e.g., long-distance running, cycling) and supports muscle repair post-training. Studies show that supplementation with the product analogues can improve mitochondrial energy production, allowing athletes to sustain higher output levels for longer durations.
Research on Nutritional Metabolism
The product serves as an invaluable tool compound in nutritional metabolism research, enabling scientists to dissect the complex mechanisms underlying nutrient utilization and homeostasis. Its targeted effects on amino acid catabolism and energy metabolism make it ideal for studying how dietary components shape metabolic outcomes in both animal models and human subjects.
In preclinical research, the product is used to investigate the interplay between dietary composition and metabolic health. Researchers incorporate graded levels of the product into experimental diets to observe its impact on key metabolic pathways, such as glucose regulation, lipid oxidation, and nitrogen metabolism. For example, studies using rodent models have demonstrated how the product supplementation modulates hepatic enzyme activity, offering insights into potential strategies for managing metabolic disorders like obesity and type 2 diabetes.
Enzymatic synthesis is a method of synthesizing target compounds using the high selectivity and efficiency of biocatalysts (enzymes). The synthesis of D-Norvaline (D-deaminocellulose) through enzymatic synthesis has high stereoselectivity and low environmental impact.
For the synthesis of this substance, commonly used enzymes include transaminase (TA), amino acid dehydrogenase (AADH), etc. Transaminases can catalyze the transfer of amino groups between amino acds, thereby generating target amino acids.
Its synthesis can start with simple ketone acids, such as alpha ketovaleric acd. This compound serves as a substrate and generates modified products by introducing amino groups through enzymatic reactions.
3.1 Transaminase catalyzed reaction
The main reaction steps catalyzed by transaminases are as follows:
1. Preparation of amino donors:
Common amino donors include L-glutamate or L-alanine.
2. Preparation of reaction mixture:
Mix the substrate alpha ketovaleric acid and amino donor in buffer solution, and add an appropriate amount of transaminase.
3. Reaction conditions:
The reaction is usually carried out at an appropriate temperature (e.g. 37 ° C) and pH value (e.g. pH 7.0-8.0) to ensure optimal enzyme activity.
4. Product extraction:
After the reaction is completed, the reaction product is separated by centrifugation or filtration, and then purified by chromatography to obtain D-deaminocellulose.
C5H8O3 + C3H7NO2 → C5H11NO2 + pyruvate
C5H8O3 + C3H7NO2 → C5H11NO2 + C3H4O3
Among them, α - ketovalerate (C5H8O3) and L-alanine (C3H7NO2) are catalyzed by transaminases to form D-Normal (C5H11NO2) and pyruvate (C3H4O3).
3.2 Amino acid dehydrogenase catalyzed reaction
Another enzymatic method for synthesizing D-Normal is to use amino acd dehydrogenase. This method typically combines amino acid dehydrogenase with coenzymes (such as NADH or NADPH) to generate D-Normal through a reduction reaction.
The reaction steps are as follows:
1. Substrate preparation:
Use alpha ketovaleric acid as the substrate.
2. Preparation of reaction mixture:
Mix substrate, coenzyme (NADH or NADPH), amino acd dehydrogenase, and amino donor in buffer solution.
3. Reaction conditions:
The reaction is carried out at an appropriate temperature and pH value.
4. Product extraction:
Similarly, the reaction products are separated by centrifugation or filtration, and then purified by chromatography to obtain D-deaminocellulose.
C5H8O3 + NH3 + NADH + H + → AADH + C5H11NO2 + NAD + + H2O
C5H8O3 + NH3 + NADH + H + → AADH + C5H11NO2 + NAD + + H2O
Among them, alpha ketovaleric acid (C5H8O3), ammonia (NH3), coenzyme NADH, and proton (H+) are catalyzed by amino acid dehydrogenase to generate D-Normal (C5H11NO2), coenzyme NAD+, and water (H2O).
In order to increase the yield and purity of D-deaminocellulose, it is necessary to optimize the reaction conditions, including:
1. Enzyme concentration:
Adjust the amount of enzyme used to achieve the best catalytic effect.
2. Substrate concentration:
Control the concentration of substrates to avoid inhibiting reactions or generating by-products.
3. Reaction time:
Determine the optimal reaction time to ensure complete reaction while avoiding enzyme inactivation caused by prolonged time.
4. Temperature and pH:
Optimize temperature and pH values to maintain enzyme activity and stability.
After the reaction is completed, a series of separation and purification steps are required to obtain high-purity D-deaminocellulose:
Centrifuge or filtration:Separate solid impurities and unreacted substrates.
Column chromatography:D-deaminocellulose is further purified using column chromatography technology to remove other by-products and impurities.
Crystallization or freeze-drying:Finally, pure D-deaminocellulose solid is obtained through crystallization or freeze-drying methods.
Finally, the purified D-Norvaline was characterized and analyzed using various analytical techniques to confirm its structure and purity. These technologies include:
1. High performance liquid chromatography (HPLC):
used to determine the purity of the product.
2. Nuclear magnetic resonance (NMR) spectroscopy:
Used to confirm chemical structure.
3. Mass spectrometry (MS):
used to determine molecular weight and structural information.
4. Optical rotation measurement:
used to determine chiral purity.
Valine, as an important branched chain amino acid, occupies a pivotal position in the field of biochemistry. And D-valine, as an isomer of valine, although its discovery process may not be as detailed as valine, it still embodies the spirit of scientists' unremitting exploration and discovery.
The discovery of valine can be considered an important milestone in biochemical research. As early as 1856, scientist Von Group Besanez first isolated this amino acid from pancreatic extract. This discovery not only reveals the rich amino acd composition in the pancreas, but also lays a solid foundation for subsequent research on amino acds.
However, at this time, valine has not been clearly named and thoroughly studied. Until 1879, scientists once again isolated valine from albumin, which further confirmed the widespread presence and importance of valine in living organisms. However, even so, the specific structure and properties of valine are still unknown.
The outstanding contribution of H. Emil Fisher led to a decisive step in the study of valine. Fisher successfully isolated valine from casein and elucidated its structure -2-amino-3-methylbutyric acd - through chemical methods. This discovery not only reveals the chemical nature of valine, but also provides important references for subsequent research on the structure and function of amino acds. At the same time, Fisher also named this amino acid "valine", which is derived from the herb Valerian, symbolizing the unique role and importance of valine in living organisms.
Adverse reactions
The product is a non naturally occurring D-type amino acid with the chemical formula C ₅ H ₁₁ NO ₂ and a molecular weight of 117.15 g/mol. Its structure is similar to natural L-type amino acids, but its spatial configuration is opposite, which may lead to significant differences in its biological activity and metabolic pathways compared to natural amino acids. As an energy supplement or exercise nutrient ingredient, the product is believed to affect the secretion of synthetic metabolic hormones, fuel supply during exercise, and mental performance in stress-related tasks, and may prevent muscle damage caused by exercise.
Digestive system response
D-Novalin may directly stimulate the gastrointestinal mucosa, causing symptoms such as nausea, vomiting, abdominal pain, and diarrhea. This reaction is more common in oral supplements and may depend on the dosage. Long term or excessive intake may increase the burden on the gastrointestinal tract, leading to indigestion or damage to the gastric mucosa. As a non natural amino acid, D-demethyl selenide may interfere with normal amino acid metabolism pathways.
Neural response
Overdosing on D-novalin may lead to excessive neuronal excitation, causing symptoms such as headaches, dizziness, insomnia, or anxiety. Long term high-dose use may increase the risk of peripheral neuropathy, manifested as sensory abnormalities (such as numbness, tingling), muscle weakness, or reduced reflexes. This reaction is more likely to occur in individuals infected with HIV or those who also use other neurotoxic drugs (such as certain antiviral drugs), indicating that D-norovirus may have potential neurotoxic cumulative effects.
Allergic Reaction
D-Novalin may act as a signal to trigger an immune response, leading to skin allergy symptoms such as rash, itching, urticaria, or erythema. Severe allergic reactions, such as angioedema and laryngeal edema, are rare but may be life-threatening and require immediate medical treatment. Some people may experience systemic allergic symptoms, including fever, chills, joint pain, or lymph node enlargement. This type of reaction may be related to the deposition of immune complexes or cytokine release, and further confirmation is required through allergen testing and immunological examination.
Liver toxicity
D-Novaline may cause liver cell damage by interfering with liver metabolic enzymes such as cytochrome P450 or triggering oxidative stress. Clinical manifestations include elevated transaminase levels (ALT, AST), jaundice, or liver discomfort. Long term use may increase the risk of fatty liver, hepatitis, and even liver failure. As an exogenous amino acid, D-Novaline needs to be excreted through the kidneys. Excessive intake may increase the renal filtration burden, leading to elevated serum creatinine, proteinuria, or vascular damage. Patients with renal insufficiency should use it with extra caution.
FAQ
What is the drug norvaline used for?
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Supplemental D-norvaline is marketed for its ability to boost nitric oxide production, enhancing blood flow and athletic endurance. Its structural mimicry of valine may also influence muscle protein synthesis.
What is DL valine used for?
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Dl-valine is the stereoisomer of l-valine and is widely used as a nutritional enhancer due to its low cost and safety. As one of the limiting amino acids in goose meat, dl-valine holds potential as a gel enhancer for goose meat and derived products.
Is norvaline an amino acid?
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Norvaline (abbreviated as Nva) is an amino acid with the formula CH3(CH2)2CH(NH2)CO2H. The compound is a structural analog of valeric acid and also an isomer of the more common amino acid valine. Like most other α-amino acids, norvaline is chiral. It is a white, water-soluble solid.
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